## N-methylacetamide cation, CH3C=ON+CH3

 H6 H5 \ / H7 - C4 | N3 / | O1 = C2 H10 \ / C8 - H9 / H11
The ion charge is 1.

## Atomic Charges and Dipole Moment

O1 charge=-0.108
C2 charge= 0.595
N3 charge=-0.148
C4 charge=-0.174
H5 charge= 0.248
H6 charge= 0.221
H7 charge= 0.168
C8 charge=-0.518
H9 charge= 0.245
H10 charge= 0.235
H11 charge= 0.234
with a dipole moment of 9.56001 Debye

## Bond Lengths:

between O1 and C2: distance=1.262 ang___ between O1 and N3: distance=1.864 ang___
between C2 and N3: distance=1.365 ang___ between C2 and C4: distance=2.471 ang___
between C2 and C8: distance=1.456 ang___ between N3 and C4: distance=1.414 ang___
between C4 and H5: distance=1.129 ang___ between C4 and H6: distance=1.109 ang___
between C4 and H7: distance=1.103 ang___ between C8 and H9: distance=1.110 ang___
between C8 and H10: distance=1.106 ang___ between C8 and H11: distance=1.102 ang___

## Bond Angles:

for N3-C2-O1: angle=90.26 deg___ for C4-N3-C2: angle=125.4 deg___
for H5-C4-N3: angle=100.7 deg___ for H6-C4-N3: angle=110.2 deg___
for H7-C4-N3: angle=117.0 deg___ for C8-C2-O1: angle=133.7 deg___
for H9-C8-C2: angle=108.1 deg___ for H10-C8-C2: angle=110.8 deg___
for H11-C8-C2: angle=110.3 deg___

## Bond Orders (Mulliken):

between O1 and C2: order=1.573___ between O1 and N3: order=0.500___
between C2 and N3: order=1.049___ between C2 and C4: order=0.055___
between C2 and C8: order=0.829___ between N3 and C4: order=0.916___
between C4 and H5: order=0.847___ between C4 and H6: order=0.905___
between C4 and H7: order=0.954___ between C8 and H9: order=0.924___
between C8 and H10: order=0.926___ between C8 and H11: order=0.960___

## Best Lewis Structure

The Lewis structure that is closest to your structure is determined. The hybridization of the atoms in this idealized Lewis structure is given in the table below.

### Hybridization in the Best Lewis Structure

1. A bonding orbital for O1-C2 with 1.9807 electrons
__has 66.32% O 1 character in a sp2.59 hybrid
__has 33.68% C 2 character in a sp2.93 hybrid

2. A bonding orbital for O1-C2 with 1.9849 electrons
__has 77.14% O 1 character in a s0.12 p3 hybrid
__has 22.86% C 2 character in a s0.11 p3 hybrid

3. A bonding orbital for O1-N3 with 1.9268 electrons
__has 77.78% O 1 character in a p3 hybrid
__has 22.22% N 3 character in a p3 hybrid

4. A bonding orbital for C2-N3 with 1.9422 electrons
__has 40.37% C 2 character in a sp2.47 hybrid
__has 59.63% N 3 character in a sp2.26 hybrid

5. A bonding orbital for C2-C8 with 1.9945 electrons
__has 53.93% C 2 character in a sp1.35 hybrid
__has 46.07% C 8 character in a sp2.99 hybrid

6. A bonding orbital for N3-C4 with 1.9836 electrons
__has 63.24% N 3 character in a sp1.75 hybrid
__has 36.76% C 4 character in a s0.97 p3 hybrid

7. A bonding orbital for C4-H5 with 1.9032 electrons
__has 63.16% C 4 character in a s0.83 p3 hybrid
__has 36.84% H 5 character in a s orbital

8. A bonding orbital for C4-H6 with 1.9646 electrons
__has 63.85% C 4 character in a sp2.89 hybrid
__has 36.15% H 6 character in a s orbital

9. A bonding orbital for C4-H7 with 1.9944 electrons
__has 61.95% C 4 character in a sp2.52 hybrid
__has 38.05% H 7 character in a s orbital

10. A bonding orbital for C8-H9 with 1.9539 electrons
__has 63.73% C 8 character in a s0.94 p3 hybrid
__has 36.27% H 9 character in a s orbital

11. A bonding orbital for C8-H10 with 1.9677 electrons
__has 63.03% C 8 character in a s0.99 p3 hybrid
__has 36.97% H10 character in a s orbital

12. A bonding orbital for C8-H11 with 1.9807 electrons
__has 64.04% C 8 character in a sp2.79 hybrid
__has 35.96% H11 character in a s orbital

18. A lone pair orbital for O1 with 1.9851 electrons
__made from a sp0.48 hybrid

19. A lone pair orbital for N3 with 1.9040 electrons
__made from a sp2.04 hybrid

146. A antibonding orbital for O1-C2 with 0.1402 electrons
__has 22.86% O 1 character in a s0.12 p3 hybrid
__has 77.14% C 2 character in a s0.11 p3 hybrid

147. A antibonding orbital for O1-N3 with 0.1817 electrons
__has 22.22% O 1 character in a p3 hybrid
__has 77.78% N 3 character in a p3 hybrid

-With core pairs on: O 1 C 2 N 3 C 4 C 8 -

#### Donor Acceptor Interactions in the Best Lewis Structure

The localized orbitals in your best Lewis structure can interact strongly. A filled bonding or lone pair orbital can act as a donor and an empty or filled bonding, antibonding, or lone pair orbital can act as an acceptor. These interactions can strengthen and weaken bonds. For example, a lone pair donor->antibonding acceptor orbital interaction will weaken the bond associated with the antibonding orbital. Conversly, an interaction with a bonding pair as the acceptor will strengthen the bond. Strong electron delocalization in your best Lewis structure will also show up as donor-acceptor interactions.
Interactions greater than 20 kJ/mol for bonding and lone pair orbitals are listed below.

The interaction of bonding donor orbital, 3, for O1-N3 with the antibonding acceptor orbital, 145, for O1-C2 is 84.1 kJ/mol.

The interaction of bonding donor orbital, 3, for O1-N3 with the second antibonding acceptor orbital, 146, for O1-C2 is 27.0 kJ/mol.

The interaction of bonding donor orbital, 3, for O1-N3 with the antibonding acceptor orbital, 148, for C2-N3 is 47.1 kJ/mol.

The interaction of bonding donor orbital, 3, for O1-N3 with the antibonding acceptor orbital, 149, for C2-C8 is 111. kJ/mol.

The interaction of bonding donor orbital, 4, for C2-N3 with the antibonding acceptor orbital, 147, for O1-N3 is 128. kJ/mol.

The interaction of bonding donor orbital, 7, for C4-H5 with the antibonding acceptor orbital, 147, for O1-N3 is 122. kJ/mol.

The interaction of bonding donor orbital, 8, for C4-H6 with the antibonding acceptor orbital, 147, for O1-N3 is 38.7 kJ/mol.

The interaction of bonding donor orbital, 10, for C8-H9 with the antibonding acceptor orbital, 145, for O1-C2 is 30.1 kJ/mol.

The interaction of bonding donor orbital, 10, for C8-H9 with the second antibonding acceptor orbital, 146, for O1-C2 is 30.9 kJ/mol.

The interaction of bonding donor orbital, 11, for C8-H10 with the second antibonding acceptor orbital, 146, for O1-C2 is 50.2 kJ/mol.

The interaction of bonding donor orbital, 12, for C8-H11 with the antibonding acceptor orbital, 148, for C2-N3 is 41.3 kJ/mol.

The interaction of lone pair donor orbital, 18, for O1 with the antibonding acceptor orbital, 149, for C2-C8 is 21.5 kJ/mol.

The interaction of lone pair donor orbital, 19, for N3 with the second antibonding acceptor orbital, 146, for O1-C2 is 104. kJ/mol.

The interaction of lone pair donor orbital, 19, for N3 with the antibonding acceptor orbital, 153, for C4-H7 is 28.2 kJ/mol.

The interaction of the second antibonding donor orbital, 146, for O1-C2 with the antibonding acceptor orbital, 145, for O1-C2 is 44.0 kJ/mol.

## Molecular Orbital Energies

The orbital energies are given in eV, where 1 eV=96.49 kJ/mol. Orbitals with very low energy are core 1s orbitals. More antibonding orbitals than you might expect are sometimes listed, because d orbitals are always included for heavy atoms and p orbitals are included for H atoms. Up spins are shown with a ^ and down spins are shown as v.

23 ----- -3.201

22 ----- -4.035

21 ----- -8.722

20 ----- -11.21

19 -^-v- -13.35

18 -^-v- -14.51

17 -^-v- -15.39

16 -^-v- -15.76

15 -^-v- -16.51

14 -^-v- -16.87

13 -^-v- -18.08

12 -^-v- -18.44

11 -^-v- -18.73

10 -^-v- -19.63

9 -^-v- -23.74

8 -^-v- -25.18

7 -^-v- -29.08

6 -^-v- -34.54

5 -^-v- -272.5

4 -^-v- -273.6

3 -^-v- -276.6

2 -^-v- -386.5

1 -^-v- -514.8

## Total Electronic Energy

The total electronic energy is a very large number, so by convention the units are given in atomic units, that is Hartrees (H). One Hartree is 2625.5 kJ/mol. The energy reference is for totally dissociated atoms. In other words, the reference state is a gas consisting of nuclei and electrons all at infinite distance from each other. The electronic energy includes all electric interactions and the kinetic energy of the electrons. This energy does not include translation, rotation, or vibration of the the molecule.

Total electronic energy = -247.6068608529 Hartrees